


Bend Over Boyfriend

by sdwbf



Category: Supernatural
Genre: Anal Sex, M/M, Pegging
Language: English
Status: Completed
Published: 2012-10-28
Updated: 2012-10-28
Packaged: 2017-11-17 06:11:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,371
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/548461
Author URL: https://archiveofourown.org/users/sdwbf/pseuds/sdwbf
Summary: <blockquote class="userstuff">
              <p>Wherein Dean struggles with the concept of being a man <em>and</em> a cockslut; Sam tries to help, but fails epically; and things end up in porn. Written for <a href="http://spnkink-meme.livejournal.com/50345.html?thread=13286313#t13286313">this prompt</a> on the SPNkink_meme. For the record, my head canon is that the boys getting horizontal changes everything, but it's only AU in the eye of the beholder.</p>
            </blockquote>





	Bend Over Boyfriend

**Author's Note:**

> As mentioned in other stories, this is a sock account I use for more extreme kink meme fills, but for a time I also used it for any Dean/Sam because my other account had gone Dean/Cas. IOW, this particular story isn't all that kinky especially when one notes that the pegging is a past, fairly non-explicit event.
> 
> Posted to Live Journal Oct. 9, 2011 with the following note: Title comes from a DVD set that explored pegging – I've not seen them, but I've heard about them. Also, I actually liked _R666_. In fact, my biggest objection to the whole Lisa-Ben storyline was they hadn't done anything to establish a connection between Dean and Lisa beyond Ben. I thought and still do it would have been a much stronger storyline if it had been Cassie-Ben. But I can also see Dean going 'Ghost truck? Seriously?' hence the negative comments.

  
**Bend Over Boyfriend** by sdwbf

Dean Winchester had a lot of sex. Been a constant of his life since he discovered the delights of his tab B meeting up with a lovely lady's slot A. Jury was out if being a manwhore was a healthier way of coping with the crazytown life he led than Dad's love of booze or Sam's of constant bitching, but whatever. So yeah, sex. Since polite people didn't discuss the age up until he met Cassie Robinson.

They'd had a two-week … thing. Too short for a real relationship, but at the same time it had been the closest he'd ever come to one. Sometimes he even thought he might have kind of, sort of loved her a little. Okay, so at the time he'd loved her a lot. Had even told her the truth about himself and the 'family business.' Not the biggest surprise in his life when she'd declared him crazy and dumped his ass. Broken a major family rule as well as a common sense one when he'd spilled the 'evil things are out there' beans because he'd simply told her. No aftermath of some supernatural experience, no proof on offer, he'd merely said, 'You need to know the truth about me,' and let it all hang out. No way anyone wouldn't have thought he was crazy. But it made a great tragic-romance tale when his annoying little brother had demanded to know the backstory for their -- he still couldn't believe he ever had to put the two words together – ghost truck hunt.

After Sam got over the 'I never told Jess in two years and you told her after two weeks' indignation – and seriously, how was that Dean's fault? – the big girl had gotten all match makery on him, then sympathetic when things hadn't worked out. Except they had. Nice nostalgic tumble in the sheets and closure on something that had never set right. Because the truth wasn't quite 'fell in love and spoke too soon so lost the girl.' Came more under the heading of 'freaked the hell out and told her so she'd send me packing.' His reason for doing so still held so the reconciliation Sam had hoped for wasn't going to happen. Time -- not to mention the fucking ghost truck (no that was never going to sound right) -- had given Cassie perspective and she'd been on board for the 'nostalgia-closure' idea, so lemon pie out of lemons for everyone.

And the whipped cream topping on the side? Sam got them both a little wasted a few nights later and they'd woken up in bed together the next morning. Naked. Dried semen decorating their bodies. Not enough booze had flowed for a Winchester to get a hangover let alone a blackout, so they spent an hour or two freaking out, then added incest to their 'laws broken on a daily basis' lists.

Was great for a couple of months. All manly hand jobs and grunts of satisfaction before retiring to separate beds as befit a 'brothers with benefits' existence. And how was it he led a life where he had to keep coming up with these weird ass names? Ghost truck. Brothers with benefits. And no, he was _not_ going to use the 'relationship' word because that's what had led him down the Yellow Brick Road with Cassie. Except Sam was a sneaky bastard. Not to mention a 'big damn girl' of a romantic beneath it all, and he had to go and ambush Dean. With a kiss.

And damn what a kiss. Dean had followed Sam into their hotel room after dinner, and the sasquatch had grabbed him, pushed him up against the wall and kissed the shit out of him. Dean had … melted. Absolutely freaking 'too weak in the knees to keep standing' melted. Sammy, the bastard, had chuckled, swept him off his feet and carried him to the nearest bed. They'd gotten naked and exchanged bodily fluids all while devouring one another's mouths. Sam hadn't even let him out of the bed to sleep. Instead he'd spooned up behind Dean and cuddled him like a teddy bear. Would have sputtered and punched him one if he hadn't been so busy falling asleep in the big goof's arms.

Which brought him to round fourteen of the morning after and waking up with his brother's erection pressed up against his ass. And had he mentioned the air of anticipation filling the room more thoroughly than the massive cock would fill his hole? Sam wanted to fuck him, had since the first kiss, but after a few rounds of asked and rejected, he'd let moments like this do the talking. Dean answered the same way he always did – by rolling onto his back and kissing Sam good morning while giving him a quick hand job to put an end to the 'discussion.' Dean should live so long.

Sam loved words and talking about feelings, but he was also a master at projecting disappointment without saying anything. Dean really hated that about him, because as much as he bitched and moaned about emo-Sam, he had no defenses at all against sad-silent Sam. And the bitch knew it.

Dean had tried everything to stall off the inevitable. He'd gone from a blow job virgin to a fucking master at it within the last two weeks. Not that Sam hadn't reciprocated with enthusiasm because Gigantor had one talented mouth. The immediate 'tit for tat' on the oral action also underscored the lack of same on the desired ass sex. Bugged the hell out of Dean. Not that Sammy recognized his own 'toppiness,' but that he'd also figured out Dean wasn't … a member of the club.

Taking after his mother in the looks department, Dean had spent his whole life trying to push back against his 'prettiness.' The layered look of the 'Winchester uniform' hid the trimness of his waist and gave him a bulkier profile, while his perpetual stubble emphasized yes, he was a guy, not to mention adding a couple of years. All window dressing for the way he acted. Macho-man Dean. Never back down from a fight, quick to get in the way of danger, in-anyone's-face Dean. He worked hard at doing 100 percent manly things, while Sam walked around being all emo and one with his inner girl. So why was his little brother so damned sure Dean needed to be the fuckee instead of the fucker?

He wanted to get really pissed about the whole thing, except … Dean knew he was a bottom. Wasn't even theoretical. Sort of. All went back to Cassie and the reason he'd freaked out. She'd seen some stupid video not long before they'd met and had decided Dean was an adventurous sort of guy. They'd had a lot of fun on that front for ten days, then she'd sprung the big one on him -- she wanted to fuck him with a strap-on dildo.

Didn't know why he'd agreed other than they'd been having such a good time together. Any second thoughts had vanished when the first lubed finger had breached him. Turned him into a writhing needy mess of 'fuck me, more, harder!' He'd come so hard he'd blacked out for a couple of seconds before she'd ever touched his cock. She'd been all 'that was so hot' and 'you're such a natural cockslut you should try it with a guy,' while his brain had been screaming, 'real men do not come that way!' He supposed it was telling the 'try it with a guy' part hadn't bothered him, but at the time, he was too busy losing his shit over the not-touched part. One bottle of whisky later, he had the 'welcome to the world of a hunter' talk with her.

Now Sam wanted his ass, and, damn, Dean wanted to give it to him. But what would Sam think of him if history repeated itself? He had to be Sam's partner, the one Sam trusted to watch his back, not someone tossed into the category of 'pretty cockslut,' then discarded when a man was needed. The fear of that rejection kept him and Sam as miserable as two young men getting regular sex, not to mention snuggles, could be. In other words, not. But frustrated, yeah.

Went on like that for another month, then Dean came out of the bathroom after showering and found the room empty. "Sam?" he called, but didn't get an answer. He frowned. They'd planned to go out to dinner to celebrate a successful salt-and-burn, and, being a gracious big brother, he'd let Sam go first. Was starting to get pissed when he noticed his best jeans and a pale green button-down on the bed. "What am I? A freaking Barbie?" he muttered, but dressed in the clothes laid out for him.

Once he'd pulled on the dress boots he normally wore with his FBI monkey suit, he glared at the world in general and snapped, "All right where the hell are you?"

A knock on the door answered him. Rolling his eyes, Dean jerked it open to find Sam standing on the other side, also dressed in his casual best. Stupid smoking hot younger brothers. "What?" he snapped when Sam grinned.

"You look beautiful when you're all flustered."

"Shut. Up."

Grin only broadened. "Come on, gorgeous, we've got reservations and a steak with your name on it." Having offered the beefy bait, Sam also offered his arm.

Dean upped the wattage of his glare, then stalked off to the Impala. Would have left the giggling goof in the dust if he'd know where the stupid restaurant was. Only took a few minutes after getting there to decide he should have gone with his first impulse. All evening Sam made it clear who the real 'girl' in their relationship was.

When they followed the hostess to their table, Sam had his hand on the small of Dean's back, then held the chair for him. He went for the total 'full on chauvinist pig' treatment and ordered Dean's meal, only stopping short of cutting the steak for him. Dean hissed and sputtered, even kicked him under the table a couple of times, but there was a limit to what he could do in a crowded restaurant, and Sam was relentless.

Almost as if to mock him further, his eyes burned with angry tears. What had he done? He'd spent months denying what he'd wanted just to keep this from happening only to lose Sam's respect anyway. Worse, he couldn't think of a way to fix it. Even if they never had sex again, they'd crossed a line that could never be uncrossed.

Sam's hand covered his, then gripped it when he tried to pull away. "I'm sorry, I'm doing this all wrong."

"Doing what? Humiliating me?" he hissed.

"No!" Sam said loud enough to draw attention from the nearby tables. He flushed, then had the nerve to look frustrated. "I wanted to show you I could trust you to watch my back no matter what you need when we're together."

Dean stared at him for a long minute uncertain whether he should laugh, cry or punch the bitch. He was leaning towards punching him when the waitress set a piece of awesome looking apple pie in front of him. Deciding retreat into pie was the better part of not making a scene, he tucked into it and found it tasted even better than it looked. That and a great cup of coffee mellowed him enough to say, "Just so you know, you're not getting anything tonight. We'll," ugh, "talk about the other thing tomorrow."

Sam nodded, then proved he was a 'brave if sometimes not too bright' bastard and reached for Dean's hand again. He considered stabbing him with his fork, but figured the blood would make the pie taste funky and let him hold his freaking hand.

True to his word, Dean didn't put out when they got back the hotel, but Sam had bought him pie, so he let him spoon up against his back.

When he woke up the next morning with the usual impressive length nestled in his crack, he studied the far wall for wisdom. Stupid wallpaper held out on him. Whatever. No way he was going to have this conversation with a full bladder and morning breath. He gave the arm draped around his waist a reassuring pat, then hopped out of bed and into the shower.

If his life were the chick-flick it kept trying to pretend it was, Sam would have joined him in the shower. But those stupid movies never took into account the limitations of the shower-size in even a decent motel. Barely room for him let alone adding Gigantor into the mix. Best nod he could make to porn, or romance if it came down to it, was to move through his morning routine with speed, then hand over the facilities to Sam.

That left him with some alone-time with the 'musical' accompaniment of the shower. Despite a list of bad-calls a mile long Sam had made last night, his little brother had made his point as well. The deeper they went into this … thing … okay, fine, relationship, the … softer Dean got. Even last night, much as he'd hated the over-kill, a part of him had liked Sam's attempt to make him feel special. Loved maybe. And yes, ladies and gentlemen, Dean Winchester had officially lost it. He actually was entertaining the idea his brother might be in love with him when most of the time he figured Sam really, really didn't even like him.

Didn't stop him from dropping the towel he'd wrapped around his waist and retrieving the bottle of lube his ever hopeful brother had taken to carrying around. Maybe the thing with Cassie had been a one off. Maybe it had been the shock of something new. Told himself that and a few other dozen hopeful lies as he slicked up his fingers and went to work loosening his hole. Might have been a more convincing set of lies if he hadn't almost come every single freaking time he slipped a finger inside.

The shower shut off and a near-lifetime of experience told him exactly how much time he had before his squeaky clean brother emerged from the bathroom. He finished getting himself ready, then wiped his fingers off on his discarded towel. With a heavy sigh, he settled face down on the bed, stuffing a pillow under his hips to lift his ass up. Hoped it would serve as both an invitation and a turn on, but it just made him feel stupid.

Might have changed his mind and gotten dressed, but he'd been careful not to 'assume the position' until he knew Sam was a second from walking into the room, and right on schedule the bathroom door opened.

"Jesus," Sam murmured and it sure sounded like 'hell, yes' versus 'oh, gross, put your pants back on.' Encouraging sign. An even better one was his brother stretching out on top of him while kissing his way up Dean's spine. "You sure, baby?"

Baby? Sam was going to call him freaking 'baby?' Kill him now because he kind of liked it. Fuck. He'd lost his mind. And the only other thing he was sure of was, "I'll come like a girl."

Sam had reached his neck, but stopped kissing long enough to ask, "What?"

Damn it, why did he always have to spell things out for Sammy? "I don't need my cock jacked to come when I'm getting fucked in the ass."

Sam's arms tightened around him with enough strength to make him gasp. "How many-?"

Jealous? Dean was dismantling his psyche and Sam was getting all caveman on him. Fuck his life anyway. "Oh, for God's sake, you're the first 'real boy,' okay?"

"How …? Oh, Cassie?" Finally he shows signs of that big brain he was supposed to have. Thank fuck he didn't have to have that conversation.

"Yes."

"That's kind of hot."

How was this his life? "Damnit, Sam, either fuck me or shoot me."

Sam chuckled, and any hope of his confession not turning reality vanished as he heard the pop of the lube bottle opening. "I already-"

"Yeah, love that, but still gonna play."

Damnit! "Sa…," his brother's name turned into a long, low moan as a finger slipped inside. By the time two breached him, he'd pulled his knees beneath him and reared back to impale himself harder and faster. Was practically sobbing when Sam went for four fingers instead of using his cock. "Please," he panted. "Please, please, please."

"Shhh, baby, I've got you." The fingers pulled out, then warm hard flesh pushed into him. So much better than plastic. The mere feel of it had him on the verge, but Sam was a talented bitch and he found Dean's sweet spot on the second thrust.

Dean shouted his enthusiasm with a volume that would have gotten them kicked out of a higher class motel, his cock stribbling pre-come all over the pillow he'd used to display himself. Somehow everything he'd kept safe inside unlocked. Normally fairly quiet during sex, Dean started babbling between the moans and the almost mewling sounds. Words about loving Sam, of needing him, begging him never to leave him, to love him. Please, please, please. Couldn't stop any more than he could stay conscious when one last thrust sent fireworks coursing through his body and mind.

Only lasted for a few seconds, the sensation of Sam spurting inside his body pulling him back to awareness. Almost made him hard again. Felt so good. So right. And on that thought some of what he'd been saying poked at his brain. No, he'd ruined it. Spilled all his needy, emo crap all over the bed and ruined it. He tried to squirm out from underneath Sam, wanting, needing to make a run for it, but, to his surprise, Sam held him tight.

"Forget it," his brother growled in his ear. "You're mine."

He was? He swallowed hard and managed to get out, "I am?"

Sam rolled away from the wet spot, pulling Dean with him, then around so they were resting chest-to-chest with Dean sprawled on top of him. "Damn right you are." He began running a hand slowly up and down Dean's spine. "Wanted you since my first wet dream. Now that I've got you I'm never letting you go."

Oh. "You don't think I'm some sort of wuss?"

Sam snorted. "I think you're the sexiest badass that ever called himself a hunter." Sam hugged him. "No one else I'd want watching my back. No one else's backside I'd rather own."

Dean blushed and snorted at the same time. Really shouldn't like the sound of that half as much as he did, but there was a principle involved here. "Not your property."

"Sure you are. I own your heart. Just like you own mine."

"I may be sick," he muttered, but relaxed against the brick wall his brother called a chest. "You really think –?"

Apparently Sam had reached his 'reassure the psycho' limit because his big hand slammed down on Dean's ass. Hurt like a bitch and Dean yelped, bucking up against Sam's hold, but Sam held on and rolled them once more so he was looming up over Dean. "I think you are an insecure bundle of mush who not only needs but deserves to be cherished everyday for the rest of our lives. I think you are the best hunter alive and otherwise. I think you're my partner in and out of this bed and how you like to have sex or come doesn't change anything else I think. But most of all I _know_ you're the love of my life and I'm never letting you go. Clear?"

Dean nodded. "Clear."

"Now spread your legs, beautiful. I want to see your face when you make that mewing sound again."

"Bitch," Dean muttered, but got his legs out of the way.

"Jerk," Sam answered, and shoved inside. That was the moment Dean would always remember. That was when he finally believed.

end


End file.
